CN101429170B - 联芳基杂环化合物的制备和用途 - Google Patents

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Publication number

CN101429170B

CN101429170B CN200810185656.XA CN200810185656A CN101429170B CN 101429170 B CN101429170 B CN 101429170B CN 200810185656 A CN200810185656 A CN 200810185656A CN 101429170 B CN101429170 B CN 101429170B

Authority

CN

China

Prior art keywords

milliliters

mmole

milligrams

mmoles

compound

Prior art date

2003-06-03

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Expired - Fee Related

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• -1 Biaryl heterocyclic compounds Chemical class 0.000 title claims description 168
• 238000002360 preparation method Methods 0.000 title description 42
• 150000001875 compounds Chemical class 0.000 claims abstract description 268
• 150000003839 salts Chemical class 0.000 claims description 36
• 239000000126 substance Substances 0.000 claims description 36
• 229910052760 oxygen Inorganic materials 0.000 claims description 23
• 229910052801 chlorine Inorganic materials 0.000 claims description 20
• 229910052739 hydrogen Inorganic materials 0.000 claims description 12
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
• 229910052731 fluorine Inorganic materials 0.000 claims description 10
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 9
• 125000000304 alkynyl group Chemical group 0.000 claims description 5
• 229910052794 bromium Inorganic materials 0.000 claims description 5
• 229910052740 iodine Inorganic materials 0.000 claims description 5
• 239000003937 drug carrier Substances 0.000 claims 1
• 239000008194 pharmaceutical composition Substances 0.000 claims 1
• 239000003795 chemical substances by application Substances 0.000 abstract description 39
• 230000002924 anti-infective effect Effects 0.000 abstract description 11
• 230000001028 anti-proliverative effect Effects 0.000 abstract description 7
• 239000002260 anti-inflammatory agent Substances 0.000 abstract description 5
• 239000002325 prokinetic agent Substances 0.000 abstract description 5
• 230000003110 anti-inflammatory effect Effects 0.000 abstract description 4
• 125000005841 biaryl group Chemical group 0.000 abstract 1
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 348
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 235
• 239000000243 solution Substances 0.000 description 229
• 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 228
• 230000015572 biosynthetic process Effects 0.000 description 217
• 238000003786 synthesis reaction Methods 0.000 description 213
• 239000000203 mixture Chemical class 0.000 description 204
• 239000011541 reaction mixture Substances 0.000 description 201
• 238000000034 method Methods 0.000 description 192
• 238000003756 stirring Methods 0.000 description 177
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 159
• 230000008569 process Effects 0.000 description 144
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 142
• 150000001412 amines Chemical class 0.000 description 130
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 123
• 238000004809 thin layer chromatography Methods 0.000 description 97
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 95
• 235000019439 ethyl acetate Nutrition 0.000 description 84
• 239000007787 solid Substances 0.000 description 79
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 79
• 239000002585 base Substances 0.000 description 74
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 73
• 238000003818 flash chromatography Methods 0.000 description 73
• 150000003852 triazoles Chemical class 0.000 description 73
• 239000011734 sodium Substances 0.000 description 68
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 66
• XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 64
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 64
• 150000001299 aldehydes Chemical class 0.000 description 61
• 238000010828 elution Methods 0.000 description 59
• 230000002194 synthesizing effect Effects 0.000 description 59
• 239000000047 product Substances 0.000 description 58
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 57
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 55
• 238000001035 drying Methods 0.000 description 55
• 238000006243 chemical reaction Methods 0.000 description 53
• 239000012141 concentrate Substances 0.000 description 50
• 125000003831 tetrazolyl group Chemical group 0.000 description 50
• 239000000284 extract Substances 0.000 description 49
• 239000002904 solvent Substances 0.000 description 46
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
• 239000000725 suspension Substances 0.000 description 43
• 239000010410 layer Substances 0.000 description 38
• 239000000843 powder Substances 0.000 description 38
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 35
• 239000007864 aqueous solution Substances 0.000 description 35
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 34
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 34
• 239000007789 gas Substances 0.000 description 33
• 150000002460 imidazoles Chemical class 0.000 description 33
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 32
• 239000003513 alkali Substances 0.000 description 32
• 229910052786 argon Inorganic materials 0.000 description 32
• UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 32
• 150000003462 sulfoxides Chemical class 0.000 description 32
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 31
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 30
• 238000001914 filtration Methods 0.000 description 29
• 239000000543 intermediate Substances 0.000 description 29
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
• 150000002148 esters Chemical class 0.000 description 28
• 238000004587 chromatography analysis Methods 0.000 description 27
• 239000012321 sodium triacetoxyborohydride Substances 0.000 description 27
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 26
• 125000004429 atom Chemical group 0.000 description 26
• 239000003814 drug Substances 0.000 description 26
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 25
• 239000000460 chlorine Substances 0.000 description 25
• 125000000623 heterocyclic group Chemical group 0.000 description 25
• 229920006395 saturated elastomer Polymers 0.000 description 25
• 229910052799 carbon Inorganic materials 0.000 description 24
• IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 24
• 229910052757 nitrogen Inorganic materials 0.000 description 24
• 239000000741 silica gel Substances 0.000 description 23
• 229910002027 silica gel Inorganic materials 0.000 description 23
• 229960001866 silicon dioxide Drugs 0.000 description 23
• RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 22
• PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 22
• 238000010992 reflux Methods 0.000 description 22
• 238000005160 1H NMR spectroscopy Methods 0.000 description 21
• 239000012044 organic layer Substances 0.000 description 20
• 229940002612 prodrug Drugs 0.000 description 20
• 239000000651 prodrug Substances 0.000 description 20
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 19
• 239000008346 aqueous phase Substances 0.000 description 19
• 238000010790 dilution Methods 0.000 description 19
• 239000012895 dilution Substances 0.000 description 19
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
• 239000002253 acid Substances 0.000 description 18
• 238000005859 coupling reaction Methods 0.000 description 17
• 238000004807 desolvation Methods 0.000 description 17
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 16
• 239000007810 chemical reaction solvent Substances 0.000 description 16
• 239000001301 oxygen Substances 0.000 description 16
• 150000003233 pyrroles Chemical class 0.000 description 16
• 210000001519 tissue Anatomy 0.000 description 16
• 238000011282 treatment Methods 0.000 description 16
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 15
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 15
• 239000000376 reactant Substances 0.000 description 15
• 238000005406 washing Methods 0.000 description 15
• 238000004128 high performance liquid chromatography Methods 0.000 description 14
• 239000007788 liquid Substances 0.000 description 14
• 239000000463 material Substances 0.000 description 14
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 14
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
• 235000015320 potassium carbonate Nutrition 0.000 description 14
• 238000012746 preparative thin layer chromatography Methods 0.000 description 14
• 238000006268 reductive amination reaction Methods 0.000 description 14
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
• LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 13
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 13
• UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 13
• 239000005864 Sulphur Substances 0.000 description 13
• 230000008878 coupling Effects 0.000 description 13
• 238000010168 coupling process Methods 0.000 description 13
• 230000000694 effects Effects 0.000 description 13
• 239000012266 salt solution Substances 0.000 description 13
• 229930192474 thiophene Natural products 0.000 description 13
• 150000001345 alkine derivatives Chemical class 0.000 description 12
• 125000002837 carbocyclic group Chemical group 0.000 description 12
• 239000012230 colorless oil Substances 0.000 description 12
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
• 238000001704 evaporation Methods 0.000 description 12
• 230000008020 evaporation Effects 0.000 description 12
• 150000002825 nitriles Chemical class 0.000 description 12
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
• 125000004076 pyridyl group Chemical group 0.000 description 12
• 229940043279 diisopropylamine Drugs 0.000 description 11
• 238000000605 extraction Methods 0.000 description 11
• CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 11
• QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 11
• FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 11
• 239000004327 boric acid Substances 0.000 description 10
• 150000001721 carbon Chemical group 0.000 description 10
• 201000010099 disease Diseases 0.000 description 10
• XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 10
• 208000015181 infectious disease Diseases 0.000 description 10
• 239000012074 organic phase Substances 0.000 description 10
• 150000003457 sulfones Chemical class 0.000 description 10
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
• NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 9
• 230000029936 alkylation Effects 0.000 description 9
• 238000005804 alkylation reaction Methods 0.000 description 9
• 229910052796 boron Inorganic materials 0.000 description 9
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 9
• 235000019341 magnesium sulphate Nutrition 0.000 description 9
• 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 9
• XCRBXWCUXJNEFX-UHFFFAOYSA-N peroxybenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1 XCRBXWCUXJNEFX-UHFFFAOYSA-N 0.000 description 9
• 230000004224 protection Effects 0.000 description 9
• KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 8
• FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 8
• 241000124008 Mammalia Species 0.000 description 8
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 8
• 239000012267 brine Substances 0.000 description 8
• 210000004027 cell Anatomy 0.000 description 8
• 210000000214 mouth Anatomy 0.000 description 8
• 125000004433 nitrogen atom Chemical group N* 0.000 description 8
• 239000003921 oil Substances 0.000 description 8
• 235000019198 oils Nutrition 0.000 description 8
• 238000001243 protein synthesis Methods 0.000 description 8
• 238000006722 reduction reaction Methods 0.000 description 8
• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
• 230000014616 translation Effects 0.000 description 8
• ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 8
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 7
• 241000894006 Bacteria Species 0.000 description 7
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
• KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 7
• 229940073608 benzyl chloride Drugs 0.000 description 7
• KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 7
• GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 7
• 239000000706 filtrate Substances 0.000 description 7
• 238000002347 injection Methods 0.000 description 7
• 239000007924 injection Substances 0.000 description 7
• 229910052763 palladium Inorganic materials 0.000 description 7
• 230000002829 reductive effect Effects 0.000 description 7
• 229910000104 sodium hydride Inorganic materials 0.000 description 7
• QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 6
• LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 6
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
• 230000010933 acylation Effects 0.000 description 6
• 238000005917 acylation reaction Methods 0.000 description 6
• 238000004440 column chromatography Methods 0.000 description 6
• JCWIWBWXCVGEAN-UHFFFAOYSA-L cyclopentyl(diphenyl)phosphane;dichloropalladium;iron Chemical compound [Fe].Cl[Pd]Cl.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1.[CH]1[CH][CH][CH][C]1P(C=1C=CC=CC=1)C1=CC=CC=C1 JCWIWBWXCVGEAN-UHFFFAOYSA-L 0.000 description 6
• 229940079593 drug Drugs 0.000 description 6
• 238000011010 flushing procedure Methods 0.000 description 6
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
• 230000002969 morbid Effects 0.000 description 6
• 210000000056 organ Anatomy 0.000 description 6
• 239000003960 organic solvent Substances 0.000 description 6
• 125000000714 pyrimidinyl group Chemical group 0.000 description 6
• 230000009467 reduction Effects 0.000 description 6
• 238000002390 rotary evaporation Methods 0.000 description 6
• 230000001225 therapeutic effect Effects 0.000 description 6
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
• 230000000699 topical effect Effects 0.000 description 6
• 239000003981 vehicle Substances 0.000 description 6
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
• MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
• 238000006069 Suzuki reaction reaction Methods 0.000 description 5
• QQAGXJMLHRUMJF-UHFFFAOYSA-N acetylene trimethylsilane Chemical group C#C.C[SiH](C)C QQAGXJMLHRUMJF-UHFFFAOYSA-N 0.000 description 5
• 230000003115 biocidal effect Effects 0.000 description 5
• 150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
• 238000006352 cycloaddition reaction Methods 0.000 description 5
• WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 5
• 238000005516 engineering process Methods 0.000 description 5
• 150000004866 oxadiazoles Chemical class 0.000 description 5
• 150000002924 oxiranes Chemical class 0.000 description 5
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
• 125000003373 pyrazinyl group Chemical group 0.000 description 5
• 125000002098 pyridazinyl group Chemical group 0.000 description 5
• 239000011347 resin Substances 0.000 description 5
• 229920005989 resin Polymers 0.000 description 5
• 239000002002 slurry Substances 0.000 description 5
• 229910052708 sodium Inorganic materials 0.000 description 5
• OXWYHTHXCLDQCN-UHFFFAOYSA-N 2-(2,3-dihydro-1,4-benzodioxin-3-ylmethyl)guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC=C2OC(CNC(=N)N)COC2=C1 OXWYHTHXCLDQCN-UHFFFAOYSA-N 0.000 description 4
• IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 4
• SFGRQCGOHCSUHP-UHFFFAOYSA-N 2-benzyl-3-phenylpropanal Chemical compound C=1C=CC=CC=1CC(C=O)CC1=CC=CC=C1 SFGRQCGOHCSUHP-UHFFFAOYSA-N 0.000 description 4
• DYDCUQKUCUHJBH-UWTATZPHSA-N D-Cycloserine Chemical compound N[C@@H]1CONC1=O DYDCUQKUCUHJBH-UWTATZPHSA-N 0.000 description 4
• KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 4
• LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
• NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 4
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
• MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 4
• OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
• XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
• 239000002168 alkylating agent Substances 0.000 description 4
• 229940100198 alkylating agent Drugs 0.000 description 4
• 150000001409 amidines Chemical class 0.000 description 4
• 238000005576 amination reaction Methods 0.000 description 4
• 235000019270 ammonium chloride Nutrition 0.000 description 4
• 230000000845 anti-microbial effect Effects 0.000 description 4
• 239000003429 antifungal agent Substances 0.000 description 4
• 239000003443 antiviral agent Substances 0.000 description 4
• 238000013459 approach Methods 0.000 description 4
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